Benzyl Alcohol → HCID 10379102, compound

HRID 1796874Notes

Reaction equation

HRID 1796874 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][CH2:14][S:15][CH2:16][CH3:17])[CH:11]([C:18]([OH:20])=[O:19])[O:10]C1(C)C)=O)(C)(C)C.[CH2:23](O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.CN(C)CCCN=C=NCC.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>ClCCl.ClCCl.CN(C=O)C>[NH2:8][C@H:12]([CH2:13][CH2:14][S:15][CH2:16][CH3:17])[CH:11]([OH:10])[C:18]([O:20][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:19]

Participants

8

Reactant 5

HCID 244Benzyl AlcoholHCID 79724-MethylmorpholineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 91593982HCID 91593982, compound

Product 1

HCID 10379102HCID 10379102, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A solution of Example 22B (0.11 g, 0.33 mmol), benzyl alcohol (0.07 mL, 0.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.080 g, 0.41 mmol), HOAT (0.045 g, 0.33 mmol), and N-methylmorpholine (0.055 mL, 0.50 mmol) in 3:1 dichloromethane/DMF (4 mL) at room temperature was stirred for 16 hours, diluted with dichloromethane, washed sequentially with aqueous NaHCO3, brine, 0.5M citric acid, and brine, dried (MgSO4), filtered, and concentrated. The residue was dissolved in 4M HCl in dioxane (2 mL), stirred for 1 hour, treated with water (1 mL), stirred for 1 hour, concentrated, and purified by reverse phase HPLC with acetonitrile/water to provide the desired product. MS (ESI) m/e 284 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 7.43–7.37 (m, 5H), 5.20 (s, 1.4H), 5.19 (m, 0.6H), 4.44 (m, 0.3H), 4.32 (m, 0.7H), 3.53 (m, 1H), 2.63 (m, 2H), 2.43 (m, 2H), 1.90–1.75 (m, 2H), 1.20–1.12 (m, 3H).

Workup

  1. washwashed sequentially with aqueous NaHCO3, brine, 0.5M citric acid, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 4M HCl in dioxane (2 mL)
  6. additiontreated with water (1 mL)
  7. stirringstirred for 1 hour
  8. concentrationconcentrated
  9. custompurified by reverse phase HPLC with acetonitrile/water

Sources & evidence

ORD record
ord-3d172d5e573546089a6459b45ad10d9d
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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